Perindopril (CED0003244)

Record Information
Version1.0
Creation Date2016-05-22 03:44:50 UTC
Update Date2026-08-20 04:17:19 UTC
Accession NumberCHEM016827
Identification
Common NamePerindopril
ClassSmall Molecule
Description
Perindopril is an organic compound with the chemical formula C19H32N2O5 and an average molecular weight of 368.47 g/mol. Perindopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. In terms of biological activity, the compound has two recorded protein targets, acting as an inhibitor of Angiotensin-converting enzyme (ACE) and Secreted frizzled-related protein 4 (SFRP4). The compound is found in or released from 18 recorded sources across multiple sectors. Within healthcare, pharmaceuticals, and veterinary products, it is associated with ACE inhibitors, lipid modifying agents, and medical devices. Other identified sources include electrical and electronic equipment—specifically batteries, capacitors, printed circuit boards, wires and cables, and cell phones—as well as synthetic textiles, carpets, and rugs. Additionally, it has been recorded in lubricants from the energy, oil, and gas sector, food packaging from the food, food processing, and cookware sector, and drinking water from the drinking water and water supply sector, among three other sectors. Recorded exposure routes for perindopril include oral, inhalation, and touch.
Contaminant Type
  • PFAS
Chemical Structure
Synonyms
ValueSource
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acidChEBI
PerindoprilumChEBI
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylateGenerator
Perindopril erbumineHMDB
Erbumine, perindoprilHMDB
PerstariumHMDB
PirindoprilHMDB
Chemical FormulaC19H32N2O5
Average Molecular Mass368.468 g/mol
Monoisotopic Mass368.231 g/mol
CAS Registry Number82834-16-0
IUPAC Name(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Traditional Nameperindopril
SMILES[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O
InChI IdentifierInChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1
InChI KeyIPVQLZZIHOAWMC-QXKUPLGCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP0.56ALOGPS
logP0.63ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity95.69 m³·mol⁻¹ChemAxon
Polarizability40 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006t-9432000000-cd5a3e77250a4c168d5fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dj-9717300000-83b70572a2f77f254c1fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-c0f0dd0396757c3cf0ceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-7900000000-6fb82e41c5f7509bf2d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0911000000-bcbd5878353663a0becfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-b7ff9447b924f0855be0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-7900000000-06fd81d1ed4113d2ccedNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-5c07491310faaef3dcb5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-f50db0738e177a896742Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0309000000-24875256bb05cbaf7142Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-4d9452d99f1522107772Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-0419000000-0e51e0565dc044821214Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2911000000-f881afe8478f809812e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-7900000000-499eef769e6c62234d00Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-1019000000-651b3131d4943a27d13dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xs-3869000000-63563bd6f1750d029d0cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ba-7920000000-49269668d5fb9b6e35b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0109000000-4e9eb37e2b101ab0d328Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0092-2933000000-3aebf3a627740b77e5adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-8900000000-f0eeabeb32b9b945d9e8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-75ed3bac35742770931bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v6r-2932000000-efd1b65151e2c1476ba7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1901000000-b8ee2f14b02c83d2d921Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2356.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
602MolluscicidesAgriculture & land managementNot Available
620Card GamesRecreation & sports surfacesNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)6.46149
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)3.81461
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)14.4021
Click to view 3D structureAngiotensin-converting enzyme 2Q5EGZ1Rattus norvegicusPredicted (SEA)27.3251
Renin structureClick to view 3D structureReninP00797HumansPredicted (SEA)255.19
Click to view 3D structureNeprilysinP08049Oryctolagus cuniculusPredicted (SEA)263.208
Procathepsin L structureClick to view 3D structureProcathepsin LP07711HumansPredicted (SEA)625.596
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)309.84
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)718.704
Cathepsin K structureClick to view 3D structureCathepsin KP43235HumansPredicted (SEA)632.758
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)1554.96
Click to view 3D structureAngiotensin-converting enzymeP09470Mus musculusPredicted (SEA)103.617
Click to view 3D structureHuman rhinovirus A proteaseQ4U254Human rhinovirus sp.Predicted (SEA)228.098
Click to view 3D structureMHC class IIQ6MGC4Rattus norvegicusPredicted (SEA)91.4728
Click to view 3D structureIgA-specific serine endopeptidase autotransporterP09790Neisseria gonorrhoeaePredicted (SEA)42.2721
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)905.309
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)929.364
Cathepsin L2 structureClick to view 3D structureCathepsin L2O60911HumansPredicted (SEA)164.807
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)2340.15
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)1838.49
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)550.628
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6293.8
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)1680.45
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)2863.68
Click to view 3D structureNS3A3EZJ3Hepatitis C virusPredicted (SEA)350.555
Concentrations
Not Available
External Links
DrugBank IDDB00790
HMDB IDHMDB0014928
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPerindopril
Chemspider ID96956
ChEBI ID8024
PubChem Compound ID107807
Kegg Compound IDC07706
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yoshiji H, Kuriyama S, Kawata M, Yoshii J, Ikenaka Y, Noguchi R, Nakatani T, Tsujinoue H, Fukui H: The angiotensin-I-converting enzyme inhibitor perindopril suppresses tumor growth and angiogenesis: possible role of the vascular endothelial growth factor. Clin Cancer Res. 2001 Apr;7(4):1073-8.
2. Hurst M, Jarvis B: Perindopril: an updated review of its use in hypertension. Drugs. 2001;61(6):867-96.
3. Simpson D, Noble S, Goa KL: Perindopril: in congestive heart failure. Drugs. 2002;62(9):1367-77; discussion 1378-9.
4. Yasumatsu R, Nakashima T, Masuda M, Ito A, Kuratomi Y, Nakagawa T, Komune S: Effects of the angiotensin-I converting enzyme inhibitor perindopril on tumor growth and angiogenesis in head and neck squamous cell carcinoma cells. J Cancer Res Clin Oncol. 2004 Oct;130(10):567-73. Epub 2004 Jul 27.
5. Jastrzebskal M, Widecka K, Naruszewicz M, Ciechanowicz A, Janczak-Bazan A, Foltynska A, Goracy I, Chetstowski K, Wesotowska T: Effects of perindopril treatment on hemostatic function in patients with essential hypertension in relation to angiotensin converting enzyme (ACE) and plasminogen activator inhibitor-1 (PAI-1) gene polymorphisms. Nutr Metab Cardiovasc Dis. 2004 Oct;14(5):259-69.
6. Parker E, Aarons L, Rowland M, Resplandy G: The pharmacokinetics of perindoprilat in normal volunteers and patients: influence of age and disease state. Eur J Pharm Sci. 2005 Sep;26(1):104-13.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24291100
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24324048
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24357222
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24511479
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24515310
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24554346
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24590580
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24602481
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24664905